1973 年 93 巻 9 号 p. 1154-1161
Configurational analyses for diastereoisomers of 3-dimethylamino-2-methyl-1-phenylpropyl phenyl ether (1a), 2-methyl-1-phenyl-3-piperidinopropyl phenyl ether (1b), 2-methyl-3-(2-methylpiperidino)-1-phenylpropyl phenyl ether (1c), and their quaternary bases were made by their nuclear magnetic resonance spectra. It was found that the chemical shifts of H(1) in the erythro-isomers appeared at a lower field and their coupling constants, JH(1)H(2), were smaller than those of the corresponding threo-isomers. The threo-amino chlorides were obtained from the erythro-amino alcohols with inversion, while erythro-amino chlorides were obtained together with threo-amino chlorides from the threo-amino alcohols. These configurational arrangements were retained in the ether condensation reactions.